Alkylalkoxymethyl esters of cresotinic acids.



. therapeutic properties,

v nrran STATES PATENT J'U'RGEN GATILSEN, OF ELBEBFELD, GERMANY, ASSIGNOR TO FARBENEABRIKEN VORM. FRIEDR. BAYER & CO., OF EL GERMANY.

BERFELD, GERMANY, A CORPORATION OF ALKYLALKOXYMETHYL ESTERS OF CR-ESOTINIC ACIDS.

No Drawing.

Specification of Letters Patent.

Application filed June 17, 1913. Serial No. 774,124.

Patented Mar. 3, 1914.

To all 007mm if; may concern Be it known that I, Jt'monN CALLSEN, doctor of philosophy, chemist, citizen of the German Empire, residing at Elberfeld, Germany, have invented new and useful Improvemeuts in Alkylalkoxymethyl Esters of Cresotinic Acids, of which the following is a specification. Y

My invention relates to the production of new pharmaceutical products which are chemically alkylalkoxymethyl esters creso'tinic acids having the following. general formula:

a v (R and R meaning alkyl radicals, such as methyl, ethyl, propyl or the like) and which, according to my researches, possess valuable being good remedies against rheumatism, an average dose being between three and ten grains for external application.

The process for producing my new compounds consists in treating salts of cresojt-inic acids with alpha-halogen-dialkylethers "having the following general formula:

(X meaning a halogen atom, R and R meaning either the same or two different alkyl radicals).

The new products are from colorless to yellowish liquids soluble in ether, alcohol, chloroform and benzene. Their alcoholic solutions are colored violet by ferric chlorid.

in carrying out my new process practically I can roceed as follows, the parts being by weig t:-1-0.85part-s of alpha-monochlorodiethylether having the formula:

I Ohemie vol. 108, p. 226) are added little by little to 19 parts of the dry sodium salt of para-cresotinic acid, while carefully cooling. After the reaction is completed, the mixture is washed with ice water and a dilute solution of sodium ear- (see Annalen cler bonate in order to remove the sodium chlorid and the excess of methyl-salicylic acid, contained therein, and subsequently dried over chlorid of calcium. 7

- The new methylethoxymethyl cresotinate of the formula:

is a yellowish oil having a faint arranatic om cmaon V coocaoa odor.

R and R meaning alkyl radicals, being'from colorless to yellowish liquids soluble in ether, alcohol, chloroform and benzene, the alcoholic solutions being colored violet by ferric chlorid and exhibiting valuable therapeutic properties, substantially as described.

2. The herein described new methylethoxymethyl ester of para' cresotinic acid of the following formula:

5 snbstantizilly as described.

1,oss,eea

a yellowish oil, breaking up into my hand ii; the presence of two subscribing JURGEN OALLSEN. Wirnesses: HELEN NWER, ALBERT NUFE-R.

sobinic acid, acetaldehyde and ethylal-i Witnesses.

001101 when reacted upon by dilute acids, and exhlbltmg valuable therapeutlc propertles,

In testimony whereof I have hereunto set 

